"I'm always genuinely surprised to win anything and I'm always grateful for it," he shares with the media backstage. "On paper and chart performance, there were certainly more worthy songs in both categories, and I think that's worth saying."

Both Dan + Shay and Aldean and Lambert also appeared in the Single of the Year category, along with Midland's "Drinkin' Problem" and Bebe Rexha's record-breaking "Meant to Be" with Florida Georgia Line.

This was the first year Stapleton claimed both the Song and Single of the Year awards, an honor he doesn't take lightly. "It's very meaningful to me because I do consider myself first and foremost a songwriter," he notes.

The country superstar won the award alongside his co-writer Mike Henderson, a man he cites as a longtime mentor. Just after their win, Henderson shared that he was one of the first people Stapleton met in Nashville after signing his publishing deal; and when the two write together, there's always a sense of ease. "To win awards with him means so very much to me that I'm not even sure I can describe it," Stapleton praises.

Since he made his official CMA Awards debut in 2015, Stapleton has experienced a domino effect of victories. He's earned a total of 10 CMAs, winning Male Vocalist of the Year four consecutive years and Album of the Year twice. While he's endlessly appreciative of the recognition, he says simply being a part of the show is reward enough.

"These things are fantastic things to win, but when you get nominated or invited to these kind of parities, in my estimation, you've already won," he explains. "You've already gotten to be far beyond anything anybody who's a musician could ever dream of getting to do, and we get to do that every day and we get to live that every day."